Regioselective and Diastereoselective Allylic Amination Using Chlorosulfonyl Isocyanate. A Novel Asymmetric Synthesis of Unsaturated Aromatic 1,2-Amino Alcohols

The diastereoselective synthesis of unsaturated aromatic 1,2-amino alcohols can be achieved on an epimeric mixture of optically active allylic ethers having a hydroxyl group attached to an allylic chiral center to the π-system using chlorosulfonyl isocyanate. These reactions produced the unsaturated anti-1,2-amino alcohols either exclusively or predominantly only for aromatic derivatives. The anti-selectivity may be explained by the Cieplak electronic model during the conversion from ethers to carbamates.